2-[3-(Methyl­diphenyl­silyl)prop­yl]isoindoline-1,3-dione

Guzei, I.A.; Spencer, L.C.; Zakai, U.I.; Lynch, D.C.

doi:10.1107/S1600536809054117

Volume 66
Part 1
Pages o221-o222
January 2010

Received 24 November 2009
Accepted 15 December 2009
Online 24 December 2009

Key indicators
Single-crystal X-ray study
T = 300 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.175
Data-to-parameter ratio = 17.6
Details

2-[3-(Methyldiphenylsilyl)propyl]isoindoline-1,3-dione

Ilia A. Guzei,^a ^* Lara C. Spencer,^a Uzma I. Zakai ^a and Daniel C. Lynch ^a

^aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, Wisconsin 53706, USA
Correspondence e-mail: iguzei@chem.wisc.edu

In the title compound, C₂₄H₂₃NO₂Si, the dihedral angle between the planes of the phenyl rings attached to the Si atom is 80.78 (10)°. In the crystal, the molecules form sheets lying perpendicular to [101] via C-HO interactions. These sheets are stacked and linked in a three-dimensional framework by additional C-HO interactions in the [10 $[\overline{1}]$ ] direction.

Related literature

For literature related to drug design see: Bains & Tacke (2003); Gately & West (2007); Guzei et al. (2010a,b); Lee et al. (1996); Tsuge et al. (1985); Yoon et al. (1991); Zakai et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2002).

Experimental

Crystal data

C₂₄H₂₃NO₂Si
M_r = 385.52
Monoclinic, C 2/c
a = 19.277 (3) Å
b = 13.238 (2) Å
c = 19.272 (3) Å
= 116.987 (6)°
V = 4382.5 (12) Å³
Z = 8
Mo K radiation
= 0.13 mm^-1
T = 300 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.964, T_max = 0.964
15551 measured reflections
4470 independent reflections
2693 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.175
S = 1.02
4470 reflections
254 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O2ⁱ	0.93	2.63	3.366 (4)	137
C14-H14AO1ⁱⁱ	0.97	2.63	3.582 (3)	169
C19-H19O2ⁱⁱⁱ	0.93	2.51	3.310 (3)	144
C22-H22O1^iv	0.93	2.32	3.200 (3)	157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 and GIS (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL, OLEX2 (Dolomanov et al., 2009) and FCF_filter (Guzei, 2007); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, modiCIFer (Guzei, 2007) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2024 ).

Acknowledgements

We thank Dr N. J. Hill (UW-Madison) for acquiring the data and Professor R. West (UW-Madison) for his support. We gratefully acknowledge Bruker sponsorship of this publication and also acknowledge grants NIH 1 S10 RRO 8389-01 and NSF CHE-9629688 for providing NMR spectrometers, and grant NSF CHE-9304546 for providing the mass spectrometer for this work.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bains, W. & Tacke, R. (2003). Curr. Opin. Drug Discov. Devel. 6, 526-543.
Bruker (2009). APEX2, GIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Gately, S. & West, R. (2007). Drug Dev. Res. 68, 156-163.
Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.
Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010a). Acta Cryst. E66, o219-o220.
Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010b). Acta Cryst. E66, o223-o224.
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Westrip, S. P. (2010). publCIF. In preparation.
Yoon, U. C., Cho, S. J., Oh, J. H., Lee, J. G., Kang, K. T. & Mariano, P. S. (1991). Bull. Korean Chem. Soc. 12, 241-243.
Zakai, U. I., Bikzhanova, G. A., Staveness, D. & West, R. (2010). Appl. Organomet. Chem. In the press.

organic compounds